


Jackson Please

by Playoff17



Category: Hannah Montana (TV)
Genre: Bondage, Feminisation, M/M, Nipple Play, PWP, Recorded, Underage Sex, Video Cameras, cockring, dub-con, gagging, non-con
Language: English
Status: Completed
Published: 2016-07-09
Updated: 2016-07-09
Packaged: 2018-07-22 10:58:04
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings, Underage
Chapters: 1
Words: 4,637
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/7434117
Author URL: https://archiveofourown.org/users/Playoff17/pseuds/Playoff17
Summary: <blockquote class="userstuff">
              <p>Jackson has had enough of Rico. So he decides to fuck him.</p>
            </blockquote>





	Jackson Please

**Author's Note:**

> *shrugs*

"You've never kissed her before have you??!! " Rico exclaimed, pointing an accusing finger at Jackson.

Look at his smug grin for God sake, Jackson thought to himself. If only he could just SLAP his little mug... two more years, he consoled himself, two more years and he wouldn't have to face it again.

"YES I DID, I did kiss her you orangutan, I even kissed her better than you ever will. Kissed her good," Jackson shot back, just as accusing.

They had now taken their argument into the living room, where Rico had the most confused frown.  
That was a new one to add to Jacksons wall of ugly Rico faces. Most of them consisted of sneers and horrible attempts at flirting that, for some reason beyond Jackson, seemed to get girls...

He set the laptop that he had been carrying under his arm down on the tea table and opened it up, seating himself on the sofa, proceeding to further Jacksons somewhat anxious curiosity.

"Why in the hell, did someone like HER-", he showed Jackson a beautiful picture of his girlfriend (a blondie he might add),"- want to date someone like THIS-".  
He then began to show Jackson a series of photographs of himself in awkward and demeaning situations. Wow, the photographer was really bad at his job, Jackson thought, as he rebuked every snarky comment on his photos to maintain his integrity. It's like the photographer particularly studied how to take the worst angles ever. He did NOT look like that in real life.

That's it. 

All of this has to stop. Now. 

Rico was not even halfway through high school yet for gods sake, and he managed to up one on Jackson in EVERYTHING, EVERY DAMN TIME. He got more girls than him, more money than him, an apparently 'funnier' personality than him.  
Just imagine that? How can someone be funnier than Jackson?

Jackson was sick and tired with this stupid game of back and forth. He didn't even think Rico had any other LEGITIMATE reason to come into his home, other than to make Jackson look stupid or a fool. He even brought props!

"Okay shut the fuck up for once!!?" Jackson yelled back at Rico, stuttering the young boy to a halt. He had begun to criticise his smell and that was going too far! Jackson took pride in his collection of designer male cologne.  
Jackson stood on the other side of the table, opposite Rico, and wow, Rico looked really small when Jackson straightened up to his full height.

"You just swore...", Rico mumbled, eyes squinting as he took in Jacksons angry demeanour.

"Yeah, I just did. I can 'fucking' say what I goddamn well please, in MY fucking house."  
With every obscene word, Rico seemed to shrink, but was somehow still holding his hostile glare at Jackson.  
Jackson wanted to wipe away every sliver and morsel of rebellion and haughtiness from this kid ever since he had first laid eyes on him.

This latino kid didn't know a single goddamn thing about Jackson. He doesn't know what Jackson gets up to in his spare time. What Jackson is capable of.

"I am fucking sick and tired of you constantly speaking back to me. Constantly questioning everything I say and do. You think I don't know a single thing about kissing cute girls huh? You think I probably haven't fucked before either don't ya?" 

Rico had positively melded himself to the sofa, the glare in his eyes faltering just slightly, and the snarky reply that he had prepared, died on his tongue.  
The laptop was still playing the snapshots that he'd collected.  
He was a bit taken aback by Jacksons sudden outburst, but in all honesty, he had been waiting for it. When you wind a sane person up like you do Jackson, you would definitely expect some sort of fuse to blow.

But Jackson right now, standing with his arms crossed, face serious, devoid of all his normal tomfoolery and clownish habits, looking like an actual angry man, kinda did wonders for Ricos confidence. He had managed to get his cute (Rico had always had a bit of a crush on him okay) employee, the most innocent and gentle hearted soul, incapable of standing up for himself, no self esteem what so ever...angry.  
This fact even seemed to stir something familiar in his groin. For some reason, he really wanted to see how far he could push it, what Jackson would do, but the logical part of his brain was telling him to back down and leave the house, right-fucking-now. But Rico's mouth and body had a life of their own apparently.

There was a heartbeat of tense silence. The corner of Ricos mouth turned up a little, into the gimmick of a smile.

"You couldn't fuck if your life depended on it." 

At that, Jacksons face immediately went devoid of all emotion. His usually cheerful eyes went dark and... another look Rico couldn't quite put his finger on, flashed across his features.  
Rico's stomach lurched at this new expression on his usually vibrant employees face. 

Jackson now looked like a man on a mission.

Rico had seemed to not only cross, but journey for miles, across a line that Jackson took quiet seriously.  
Jackson had now decided he was going to have a little fun with his bosses son, and his 'big mouth'. 

Teach him a thing or two about life.  
There was no one in the house and there wasn't going to be for another couple of hours.

"Where's your camera?" Jackson asked, voice a little deeper, more demanding, snapping out of the tense staring contest he'd unconsciously started with Rico.

"Huh?" Rico replied stupidly, his voice dry. He hadn't realised he'd been holding his breath the entire time. 

He fumbled next to him for his camcorder, just to feel if it was still there; he had no intention of giving it to Jackson. But Jackson had strode round the table, swiftly grappled the camcorder with one hand, and lifted Rico to his feet with the other, his broad palm wrapped entirely around Ricos skinny bicep.

"H-Hey!? Let go of me!" Rico struggled, but the hold got tighter and more painful. He could feel Jacksons emotionless gaze boring into the top of his head. He peered up slowly, through his black bangs, at Jacksons stone cold face. His jaw set, his lips thin, telltale signs of a beard emerging on the edges of his jaw. Jackson looked like an actual man up close, and it kind of scared the hell out of Rico.  
The muscles on Jacksons arm flexed as Rico struggled futilely, and it turned him on too, embarrassingly. He would have to have a bit of a sit down with himself after this ordeal, Rico thought to himself.

"You wanna know why that hot ass bitch goes out with me? Let me give you a first hand demonstration." Jackson began dragging Rico to the stairs as he spoke, Rico stumbling in his steps, next to Jacksons purposeful strides.

Rico couldn't believe what was happening. Either this was a really bad (or really good if he listened to the messed up side of him) dream, or Jackson was NOT referring to what Rico's pubescent mind usually associated every conversation with.  
And when did Jackson say things like 'hot ass bitch'?

He was led up the stairs and through the hallway to what he assumed to be Jacksons room.

"Jackson, calm down dude-" Rico began, eyeing Jacksons messy room warily, as he was forcefully pushed inside.  
"Shut the fuck up Rico," Jackson replied simply, locking the door to his room for extra measure.  
Rico was actually scared now. What if Jackson was planning to murder him? Well, it was a little far fetched but so was the possibility of Jackson FUCKING him, in his defence.

With the camcorder still in his hand, Jackson started towards Rico, unknowingly backing the smaller boy up against the edge of the mattress.

"Wha-", was all Rico managed to utter before he was pushed quite forcefully onto Jacksons king sized bed. He hadn't even stopped bouncing when Jackson manhandled him to lie on his back, against the pillows, with his hands being tied to the posts at the head of the bed.  
Rico was straining to see what he had even used. Was that a TIE? When did Jackson even wear ties?

"Ok, Jackson, let me go, stop it, it's not funny anymore, I get it dude, I'm sorry okay- no no wai-" Ricos voice was muffled by another piece of cloth as it was placed over his mouth. This time it was Jacksons girlfriends silk scarf she left by 'accident'.  
Rico was now kicking, and struggling against these strong knots. How the hell did Jackson know how to tie knots like that? How did Jackson even KNOW what he was doing now??  
Rico was starting to hyperventilate. This couldn't be happening. What if Jackson was planning to torture him?! There was no way Jackson could lay a finger-

"Calm down Little Rico, I'm just going to show you something okay?" Jackson was setting up a tripod and placing Ricos camcorder a foot away from the bed, so that the whole length of Rico could be seen on the screen.

He pressed 'record'.

Rico's struggling had died down into small, quick breaths, as big anxious, fearful eyes watched Jacksons every move. He saw the red light flicker on against the camcorders black body, like an intimidating robotic eye.

Jackson strode over to the bed and climbed on top, dragging out the tension, making Rico gag with the uncertain inevitability of it all.  
Jackson leaned over Rico's small frame, the boys legs clenched together, and brushed a lock of silky black hair out of his eyes.  
Rico froze at the intimacy.  
Jacksons small grin widened as something akin to a predator gazing upon its helpless prey flashed across his eyes.

Jacksons started with the boys shoes and socks and moved onto Rico's shorts, which were removed in one swift move. Rico yelled out in surprise when he felt a breeze somewhere he shouldn't be right now.

"Going commando are we? Do you always leave your panties at home little Rico? Even when your working with me?"

Rico couldn't fathom the embarrassment and humiliation he felt at that- at this. The fact that Jackson said ...panties.. was enough for Rico to feel suicidal. And as if it couldn't get any worse, he felt himself getting harder at the debasement. He didn't even wear panties... why did he feel embarrassed?

This actually looked like it was happening. And Jackson was filming it all.

Jackson grabbed Rico's skinny knees and forcefully jerked them apart. Rico yelped out in pain, not used to such force being exerted on himself. It was usually him who initiated such things on other people. He was rich, he never had to feel force. 

Nevertheless, he was laid completely bare to the carnivorous eyes of this new Jackson that honestly scared him to death but still made him shamefully hard.  
Rico closed his eyes and waited for Jackson to make fun of him, or call him 'gay' or make fun of his cock and balls.

"You might as well enjoy yourself, it's not like you'll be leaving anytime soon," Jackson mused. It didn't sound like it at all though. Rico knew perfectly well he was small for his age, but it didn't bother him much. Money gave him a few extra metaphorical inches.  
Rico opened his eyes to Jackson staring at the expanse of his legs, thighs, hips, cock and balls, the little pubic hair he had and then began to run his hands up under the shirt to reveal Rico's stomach and chest, bunching it up all the way to his collar.

Rico felt a draft come on again and shivered. His nipples hardened.

The tension was seriously having an effect on his breathing, and all the staring that Jackson was doing didn't help at all. Rico had resigned himself to the inevitability of it all, and he really now just wanted Jackson to hurry up and get it over with for heavens sake.

Rico tried to say a few words but they were muffled hopelessly. He tried to get his thought across by looking pleadingly at Jackson to let him go. He strained his hands, which were now hurting a little by the way, against the soft ropes.

Jackson looked down at Rico's feeble attempts to rid himself of the ropes. He chuckled a little to himself. He remembered that Asian girl he had dated for a few weeks, and how she introduced him to a whole new world involving ropes. He still couldn't believe classes were given about it. There was no way Rico would be able to untie himself. But Jackson also knew it wouldn't hurt too much in the long run.

He started to run his calloused hands up the expanse of Rico's lightly tanned stomach to his nipples. Soft brown nubs that had become hard from being uncovered, and the breeze blowing in through the window. Jackson started to rub his thumb over them, listening to Ricos hitched breaths and the occasional subdued moans escaping from him. He writhed his body, trying to shy away from Jacksons unashamed exploitation of his body. Jackson could see the latino turning red out of his own embarrassment. 

A feral smile played on his lips.

Rico started becoming more vocal as he moaned loudly through the silk gag. Every rub was a little more rough, causing his nipples to become more sensitive. Jacksons lightly using his thumb nails to scrape them, sending powerful waves of pleasure shooting to his dick, and he was leaking just from this. He had no idea he was so receptive to his nipples.

Jackson could clearly see the effect that he was having on Rico, and was enjoying it. But he couldn't let Rico look like he was doing this against his own will... He had to show the camera that he had actually begged Jackson to fuck him, just like he made his previous partners beg. With the camera, Jackson had hardcore evidence against Rico.

Suddenly the hands torturing his nipples disappeared, and Rico felt a brief moment of relief before a hand encased his swollen erection.  
After the nipple play, he had become quiet sensitive and very turned on, and not being able to put a hand on his cock made everything more frustrating. But now that Jackson had started to pump him very slowly, using his precum as lube, it made Rico let out a particularly wanton sound that honest to God made Jackson fully hard almost instantly.  
Deciding he wanted to skip the foreplay (the boy was already sweating, his fringe sticking to his forehead and his dick leaking, he was clearly ready), Jackson hopped off the bed and was followed by a small whimper from Rico. The latino kept his legs spread wide. He shucked off his jeans and socks, tugging his shirt over his head. 

He reached into his bedside drawer for the cherry flavour lube (requested by a girlfriend) and a condom packet. Jackson began to get himself undressed quickly and efficiently, shucking the pants and shirt and leaving them on the floor near the bed.

Jackson could feel Rico's hooded eyes run up the extent of his back, and legs.  
He turned back around so that Rico could have a good eyeful of his standing manhood. Needless to say, his eyes widened quiet comically as he realised just what Jackson had been supporting all this time. 

"Don't worry, you'll get to feel every inch of it," Jackson had such a shit eating grin, it made Rico want to use the ties currently around his wrists to strangle him.  
Rico still couldn't believe that this was happening to him. 

He watched worriedly, his breath held, as Jackson lubed himself up, and climbed on to the bed slowly. Rico knew he was making a show out of himself, prolonging the agonising wait.

It was needless to say that Rico was indeed shit scared of Jackson.

"..." Rico was trying to say something.

"Sorry? I didn't quiet catch that?" Jackson said, squirting lube onto his fingers. "If you be a good girl I'll take off the gag. Are you going to promise me that you'll be a good girl?"

Rico was feeling mortified with the response of his body to being a 'good girl' but nodded nonetheless, relieved to be finally rid of the gag filling his mouth achingly.  
Jackson tossed it somewhere to the side and observed Ricos spit coating his lips and chin, the corners of his mouth faintly red from there the silk dug in.

 

"Jackson, you don't have to do this I said I was- ahhh" Rico was surprised by the feeling of a cold wet gel on his ball sack, running down the crack of his ass and over his anus. He tilted his head to see the lube in Jacksons hand.

"Jackson, I mean it- fuuuuck, please!" Rico was again caught off guard by the sudden intrusion of a finger into his hole. And it wasn't a slow gliding entrance either.  
Jackson seemed to have thrust it in with a vengeance.

“Shit, Jackson please, at least go slow, Jackson..." Rico screwed his eyes shut, tears threatening to prickle at the corners of his eyes. His body was trying to reject the foreign intrusion, and it felt so weird having something go in rather than out. Truthfully, he had always wanted to try this but was too cowardly to.  


Rico let his head fall back as Jackson ignored his calls, much preferring to keep his eyes glued to the finger going in and out of his ass.  
He kept trying to close his legs but Jackson had a strong grip on his comparatively skinny thighs, so it was no use.  
Rico was also afraid that if he tried to yell, Jackson would gag him again. 

So he let his body go slack accepting his fate, trying to make it as easy as possible for himself. He was also trying to keep in his moans, not wanting to encourage this sadist.  
His body moved along the silk sheets, with the deep thrusts of Jacksons finger, and just as it was starting to feel a little better, Jackson, slower this time, pushed in a second finger.

Ricos eyebrows scrunched up as his mouth let out a silent whimper of pain at the stretch. It was like he was going to tear every time Jackson moved both fingers in and out.  
Thankfully, Jackson realised he needed more lube and squirted on some more, making the thrusts more fluid and easier. 

"Jackson it hurts..." Rico groaned out, his body too slack to tilt his head up to look at him. 

"If you just let yourself relax your really really going to enjoy this."

Maybe it was the way he said it, but Rico would take anything at this point to make it less painful. He closed his eyes and let his legs fall open as far as they could, let his arms dangle above him at the knots, and unclenched everything he was trying to hold together to lessen the pain.

"Well done, that's much better," Jackson responded, a slight smile in his voice. He was still thrusting wit his fingers at the same pace, but started thrusting in a little deeper, as if he was looking for something-"  
"AAAhhhhnnn!" Rico moaned loudly tis time, jerking away, the ropes on his wrists painfully digging in. A bolt of pleasure shot up his spine, threatening him to almost spill on the spot.

Jackson gripped Rico's hips as he kept stroking what was Rico's new found prostate. The boy beneath him had released all restrains on his vocals, and Jackson was amused at thought of his two old-aged neighbours hearing.  
Rico was trying hard to buck against the fingers breaching him, as a powerful orgasm coiled in his abdomen.  
And as soon as he thought he was going to explode, he felt cut off, and quiet painfully so.

"Jack-son!?" Ricos breath hitched, looking directly at the thumb and forefinger curled around the base of his cock, cutting him off from his desperate release.  
Jackson had a feral smile as he reached for something Rico couldn't see beside him. He suddenly felt something cold and incredibly tight being pulled tight around his dick, sliding and resting where Jacksons fingers where.  


"Jackson, please, no it hurts, take it off," Rico whimpered, his cock red and purple and leaking. His limbs felt heavy and sweat covered him like a second skin.

Jackson slowed his fingering, and then pulled out altogether, leaving Rico empty. Rico gasped, hips bucking again, searching for that filling. This was followed by some whimpering, and then another loud moan.  
Jackson had lifted Rico's leg and started kissing around Ricos hole, running his hand down the boys quivering thighs, before landing between his ass cheeks and spreading them.

Rico was gasping for air, the heat in his body soaring as he craved the intense release. He felt like if he stopped biting his lips he would start imploring Jackson to fuck him already and Rico was not ready to allow Jackson that pleasure..

A wet tongue started stroking around the fluttering muscle, red from Jacksons previous ministrations. He then stuck his tongue right into the clenching hole, relishing Jacksons body go taught as he made sobbing noises.

‘Jackson… please… please Jackson,’ Rico gasped out, his eyes red and tear streaked.

Jackson gave one final lick with the flat of his tongue before deciding to sit up, if not for Rico's pretty pleads, but for his growing impatience too.

Jackson moved forward until his thick cock was rubbing lengthwise over Rico's ass, catching just slightly at his hole.

‘Jackson, fuck sakes…’ Rico breathed, stomach rising and falling rapidly, as his thin arm muscles jerked on the rope at his wrists.

‘What is it that you want Rico?’ Jackson asked, watching the smaller boys face as he stared at the ceiling with hooded eyes.  
‘Jackson, just… i want to come,’ Rico began looking and sounding his age more than ever,’It seriously hurts Jackson.’

‘And how would you like me to do that Rico?’ Jackson asked, smiling at the boy. Beads of pre-come were dripping onto Rico’s ass, and Jackson used his thumb to rub them over his hole.

‘Please Jackson…’ Rico began, realising what Jackson was trying to get at.

‘Tell me how you want me to make you come,’ Jackson asked calmly, a stark contrast to the rage of conflicts going on inside Rico's body.

‘I hate… you… fuck *gulps* cock, i want you to fuck me with your cock until i come…’ Rico closed his eyes, feeling another wave of agonising pleasure and shame from his own words.

‘Thats much better, good girl.’

Jackson wasted no time pushing the head of his dick through the trembling circle of muscle. The slide of his own saliva, precome and lube making the intrusion much easier.  
Rico had to stretch twice as much, and felt as if the preparation of Jacksons fingers were almost a waste of time against the real thing.

His mouth was open silently in a gasp of pain, experiencing the slow penetration.  
It had felt like forever before Jackson was fully seated in Rico, his pelvis connecting with the latinos ass.

Jackson took some time to let Rico adjust to the undoubtedly painful obtrusion of his anus, even though his body screamed the opposite. Rico breaths started slowing down until he started shifting a little uncomfortably.  
Rico relaxed himself as he realised that it wasn't as bad if he let himself calm down a little.

Jackson started with small movements and then picked up until a few inches of his cock were gliding in and out of Rico. Rico had so far laid back and let Jackson work up his pace, before he started making noises with every thrust against his ass.

Just as Rico was about to ask him to ease up, Jackson started thrusting in and out more deeper and at a certain angle, until he again found that spot that drove Rico over the edge.

‘Ah-Ah-Ah-Jack-son, stop-aaaaah!’Rico started, his eyes fluttering shut, as another wave of pleasure rolled over him.  
‘You sure are sensitive aren't you?’ Jackson murmured, grabbing the boys hips, not relenting in his punishingly hard thrusts.  
He earned a steady roll of breathy moans, which began to get higher in pitch, before Rico started to, almost on instinct, move his hips in sync with Jackson to reach the release he knew he couldn't have yet.

‘Jackson… Jackson please take it off…’ Rico breathed, looking up at him through his sweaty bangs. Hi eyes trailed down to where his and Jacksons bodies connected at every thrust.

Rico's member was extremely stiff and an angry red, leaking globs of semen in its effort to cum. Jackson considered cumming first, just to frustrate the younger, but decided to be merciful this once and cum together.

Jackson reached down and slipped off the cock ring, earning a particularly relieved sigh. 

Jackson himself felt his release peaking powerfully as his thrusts became more erratic and the sound of skin against skin increased in volume.

The orgasm hit Rico first, causing the boy to arc up into Jackson, as his body seized up, his anus clamping down on Jacksons cock like a vice, subsequently pushing him over the edge too.

Rico blinked a few times, the intensity of the orgasm still rushing through his body in waves.

Jackson dropped down next to Rico, breathing heavily, both of them covered in sweat. Rico let out a whimper as he felt Jacksons cock slip out his sensitive puffy hole.

He pulled on the ties restraining him. Jackson lifted himself up and slipped them off one by one.

‘I hate you so much...' Rico muttered, turning his red face into the pillow, away from the camera and rubbing his wrists. Oh yeah, the camera was still filming.  
Rico couldn't believe his most intimate moment was recorded on there and Jackson had open access to it. That footage could seriously ruin everything for Rico. His parents still didn't know rico was bisexual for one.

‘Jackson, please don't release the videotape, ill do anything you want… okay,’ Rico whispered with what was left of his vocal cords. Jackson shifted until he sat beside the latino.

‘I just want you to admit something to me. Admit that i am much better at you in bed and probably everything else if i was given the chance. And that you were completely wrong about me.’

‘I was completely wrong about you, on everything, and you are much better than me in so many ways, and your fantastic in bed, and-yeah,’ Rico looked up hopefully, his eyes pleading as he repeated, unabashed, Jacksons words back to him. 

Jackson leaned down until his arms caged Rico in, and he was eye level with the younger.  
‘If you ever demean me again like you did today, not only will i upload the videotape to the internet, ill take you again like i did just moments ago, and it wont be an entirely pleasurable experience, got it?’

Rico nodded quickly, slightly terrified again.

Jackson, satisfied, climb off the bed, then padded over to the camera and stopped it recording, checking to see if everything was caught on tape. He closed the camera and slipped his jeans on, glancing behind him to see a latino already half dressed and mussing up his hair, trying to make it look as didnt-just-lose-my-virginity as possible.


End file.
